((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

Base Information

• Chemical Name: ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol
• CAS No.: 1192756-80-1
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364

Synonyms:((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

Chemical Property of ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

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Technology Process of ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

There total 1 articles about ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (96691-92-8) → ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-80-1)

Guidance literature:

(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene; With ozone; Sudan III; In methanol; dichloromethane; at -60 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at -60 - 0 ℃; Inert atmosphere;

With water; ammonium chloride; In methanol; dichloromethane;

DOI:10.1021/ol902107g

Reference yield: 88.0%

vinyl acetate (108-05-4,9003-20-7) + ((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-80-1) → ((2S,3R,4R,5S,6R)-4-(benzyloxy)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl)methyl acetate (1192757-01-9)

Guidance literature:

With Rhizomucor miehei lipase; In di-isopropyl ether; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol902107g

Reference yield: 40.0%

((2R,3S,4r,5R,6S)-4-(benzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-80-1) + acetic anhydride (108-24-7) → ((2SR,3RS,4RS,5SR,6RS)-4-(benzyloxy)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl)methyl acetate + C20H28O6

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 13h; Inert atmosphere;

DOI:10.1021/ol902107g

upstream raw materials:

(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Downstream raw materials:

((2S,3R,4R,5S,6R)-4-(benzyloxy)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl)methyl acetate

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